3DPAFIPN, or 2,4,6-Tris(diphenylamino)-5-fluoroisophthalonitrile (CAS 2260543-73-3), is a metal-free organic photocatalyst from Ossila. It belongs to the cyanoarene family of thermally activated delayed fluorescence (TADF) materials and is supplied as an unsublimed grade with purity above 98.0% by 1H NMR, in the form of a yellow powder or crystals.
Structurally, the molecule is a fluorinated isophthalonitrile core carrying three diphenylamine groups positioned meta to one another. Because diphenylamine donors are richer in electrons than carbazole units, the HOMO is destabilized and the transition energy shrinks, shifting absorption further toward the visible region than in carbazole-based relatives such as 3CzClIPN.
Working as a donor–acceptor photosensitizer, 3DPAFIPN triggers single electron transfer (SET) when illuminated with visible light. This lets chemists drive reactions under mild conditions with good energy efficiency, and it has been applied to intramolecular cyclizations and to forming C-C, C-N and C-P bonds.
- Visible-light photoredox catalysis for intramolecular cyclization reactions.
- Photocatalytic construction of C-C, C-N and C-P bonds under mild conditions.
- Gram-scale photosynthesis of heterocycles such as pyrano[2,3-d]pyrimidine and 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives.
- Organic photosensitizer for visible-light-driven CO2 reduction alongside a Mn(I) catalyst.
- Research on metal-free TADF donor–acceptor cyanoarene photocatalysts.
| Brand | Ossila |
|---|---|
| CAS number | 2260543-73-3 |
| Molecular formula | C44H30FN5 |
| Purity | Unsublimed >98.0% (1H NMR) |
| Category | — |
| Pack sizes | 250 mg, 500 mg, 1 g |
| Physical form | Yellow powder/crystals |
| Storage | — |
- Product code: M2501B1
- Full name: 2,4,6-Tris(diphenylamino)-5-fluoroisophthalonitrile
- Molecular weight: 647.74 g/mol
- Photocatalyst activation: 390 nm
- Fluorescence: λem 525 nm in acetonitrile
- HOMO/LUMO: E1/2 = -1.94 V (vs. Fc+/Fc)
- Classification / Family: Triphenylamine, Phthalonitrile, Cyanoarene, TADF materials, Photosensitizers, Photocatalysts
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